(2S,3S)-2-[2-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-2-methyl-propionylamino]-3-methyl-pentanoic acid methyl ester | 854008-70-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3S)-2-[2-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-2-methyl-propionylamino]-3-methyl-pentanoic acid methyl ester
• 英文别名: Boc-Phe-Aib-Ile-OMe；methyl (2S,3S)-3-methyl-2-[[2-methyl-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]propanoyl]amino]pentanoate
• CAS: 854008-70-1
• 化学式: C₂₅H₃₉N₃O₆
• 分子量: 477.601
• InChiKey: ZJDARLLKTXJTLG-WDSOQIARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-[2-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-2-methyl-propionylamino]-3-methyl-pentanoic acid methyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以89%的产率得到(2S,3S)-2-[2-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-2-methyl-propionylamino]-3-methyl-pentanoic acid
  参考文献：
  名称：

  Can a consecutive double turn conformation be considered as a peptide based molecular scaffold for supramolecular helix in the solid state?

  摘要：

  Helices and sheets are ubiquitous in nature. However, there are also some examples of self-assembling molecules forming supramolecular helices and sheets in unnatural systems. Unlike supramolecular sheets there are a very few examples of peptide sub-units that can be used to construct supramolecular helical architectures using the backbone hydrogen bonding functionalities of peptides. In this report we describe the design and synthesis of two single turn/bend forming peptides (Boc-Phe-Aib-Ile-OMe 1 and Boc-Ala-Leu-Aib-OMe 2) (Aib: alpha-aminoisobutyric acid) and a series of double-turn forming peptides (Boc-Phe-Aib-IIe-Aib-OMe 3, Boc-Leu-Aib-Gly-Aib-OMe 4 and Boc-gamma-Abu-Aib-Leu-Aib-OMe 5) (gamma-Abu: gamma-aminobutyric acid). It has been found that, in crystals, on self-assembly, single turn/bend forming peptides form either a supramolecular sheet (peptide 1) or a supramolecular helix (peptide 2). unlike self-associating double turn forming peptides, which have only the option of forming supramolecular helical assemblages. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.057
• 作为产物：
  描述：

  Boc-Phe-Aib-OMe 在 sodium hydroxide 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 82.0h， 生成 (2S,3S)-2-[2-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-2-methyl-propionylamino]-3-methyl-pentanoic acid methyl ester
  参考文献：
  名称：

  Can a consecutive double turn conformation be considered as a peptide based molecular scaffold for supramolecular helix in the solid state?

  摘要：

  Helices and sheets are ubiquitous in nature. However, there are also some examples of self-assembling molecules forming supramolecular helices and sheets in unnatural systems. Unlike supramolecular sheets there are a very few examples of peptide sub-units that can be used to construct supramolecular helical architectures using the backbone hydrogen bonding functionalities of peptides. In this report we describe the design and synthesis of two single turn/bend forming peptides (Boc-Phe-Aib-Ile-OMe 1 and Boc-Ala-Leu-Aib-OMe 2) (Aib: alpha-aminoisobutyric acid) and a series of double-turn forming peptides (Boc-Phe-Aib-IIe-Aib-OMe 3, Boc-Leu-Aib-Gly-Aib-OMe 4 and Boc-gamma-Abu-Aib-Leu-Aib-OMe 5) (gamma-Abu: gamma-aminobutyric acid). It has been found that, in crystals, on self-assembly, single turn/bend forming peptides form either a supramolecular sheet (peptide 1) or a supramolecular helix (peptide 2). unlike self-associating double turn forming peptides, which have only the option of forming supramolecular helical assemblages. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.057